| Saturday 7th September 1985 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Bootle | 0-1 | Chorley | Att: 125 |
| Saturday 5th October 1985 | F.A. Trophy 1st Qualifying Round | ||
|---|---|---|---|
| Bootle | 4-4 | Shepshed Charterhouse | Att: 110 |
| Tuesday 8th October 1985 | F.A. Trophy 1st Qualifying Round Replay | ||
|---|---|---|---|
| Shepshed Charterhouse | 3-1 | Bootle | Att: 498 |
| Saturday 9th November 1985 | Liverpool Senior Cup 1st Round | ||
|---|---|---|---|
| Bootle | 2-0 | Formby | |
| Wednesday 20th November 1985 | League Challenge Cup 3rd Round | ||
|---|---|---|---|
| Great Harwood Town | 2-0 | Bootle | |
| Saturday 11th January 1986 | Liverpool Senior Cup 2nd Round | ||
|---|---|---|---|
| Kirkby Town | 2-1 | Bootle | |
